多芳基氮杂氟硼二吡咯的合成及其光热性质  

Synthesis and Photothermal Properties of Polyaryl Aza-BODIPY

作　　者：李晓涵 孟祥龙 盛万乐 LI Xiaohan;MENG Xianglong;SHENG Wanle(Key Laboratory of Cancer Medical Transformation,Bengbu Medical University,Bengbu 233030,China;Anhui Laboratory of Molecule-Based Materials,Anhui Normal University,Wuhu 241001,China)

机构地区：[1]蚌埠医科大学癌症医学转化重点实验室,安徽蚌埠233030 [2]安徽师范大学安徽分子基材料重点实验室,安徽芜湖241001

出　　处：《合成化学》2024年第7期649-656,共8页Chinese Journal of Synthetic Chemistry

基　　金：蚌埠医学院自然科学基金资助项目(2022byfy006);安徽分子基材料重点实验室开放项目(fzj2208)。

摘　　要：具有较高光热效率的近红外有机染料在光热治疗领域有很好的应用前景。本文以氮杂氟硼络合物(Aza-BODIPY)作为研究对象,利用溴化反应和Suzuki偶联,合成了3种具有多芳基氮杂氟硼二吡咯化合物。探究了这3种具有多芳基Aza-BODIPY化合物的最大吸收峰以及光热性能与芳基数量的关系。结果表明:四到六芳基Aza-BODIPY在CH_(2)Cl_(2)的最大吸收峰分别为691 nm、684 nm和680 nm,这说明随着Aza-BODIPY的芳基数量增加,化合物的吸收光谱并没有明显红移。光热实验表明:多芳基Aza-BODIPY其具有较高的光热转化效率。以二甲苯作为溶剂,配制成20μg/mL的溶液,四到六芳基Aza-BODIPY光热转换效率分别为75.4%、77.3%和76.8%。说明在Aza-BODIPY的2-位和6-位引入芳基对光热效应的促进作用很有限。这可能是因为芳基数量增加会造成基团之间变得拥挤,使得基团的旋转受阻,综合表现光热效应增加不显著。本论文证明了在Aza-BODIPY的2,6-位引入芳基不能使光谱红移,可以略微地提高光热转换效率。Near-infrared organic dyes with high photothermal efficiency have a promising application in the field of photothermal therapy.In this article,we take Aza-BODIPY as the research object,and synthesize three polyarylaza BODIPY compounds by using bromination and Suzuki coupling reaction.Explore the relationship between the maximum absorption peaks and photothermal properties with the number of aromatic groups of these three Aza-BODIPY compounds.In CH_(2)Cl_(2),the maximum absorption peaks of four to six aryl Aza-BODIPY are tested to be 691 nm,684 nm and 680 nm.This results indicating that with the increase of the aryl group of Aza-BODIPY,the absorption spectrum of the compounds does not show a significant red-shifted.Photothermal experiments have shown these Aza-BODIPY compounds have high photothermal conversion efficiency.When prepared into a solution of 20μg/mL using dimethyl sulfoxide as a solvent,the photothermal conversion efficiency is 75.4%,77.3%,and 76.8%,respectively.The effect of aryl in 2,6-position of Aza-BODIPY on photothermal is limited.It may be because increase the number of aryl groups will cause the crowding between the groups,so that the rotation of the groups was blocked,and the increase of photothermal conversion efficiency was not significant.This paper proved that the introduction of aryl group at the 2,6-position of Aza-BODIPY can’t redshift the spectrum,but can slightly improve the photothermal conversion efficiency.

关 键 词：氮杂氟硼二吡咯 SUZUKI反应 近红外 吸收 光热 

分 类 号：O627.31[理学—有机化学]